Alex Weinstein
On Growth, Product, and Leadership
Strong beliefs, held loosely

As people managers, we often talk about creating an environment where each employee “feels like an owner.” We give out stock options, talk about aligned destiny (we all sink together or rise together in this startup!) and hire people who want to control their own future.  

We accept the idea of ownership as an unbiased, pure virtue; as if a team filled with an ownership mindset is an invulnerable hero in shining armor, destined to slay the awful odds of rampant startup failure. We’ve grown up on leadership books describing olden-age corporations filled with “drones,” disengaged employees who are clocking it in, present only for a paycheck and working just enough to not get fired. Surely, the opposite must be a good thing?

Is it that simple or can we hold the idea of ownership too tightly to our chests and become infatuated with the concept? The lack of balance can make us succumb to the dark side of ownership. Let’s explore what this looks like, so as to not fall into it.

The smartest people are constantly revising their understanding

A shop keeper who owns a corner store that’s been in business for a while possesses magical merchant sensibility: knowledge of the customer combined with common sense. It allows him to buy the products his customers want and stay away from extravagant moves that’ll never work. But this same approach can make the merchant risk-averse, filled with fear. When other corner shops get online and start offering online ordering and in-store pickup, he’s got to take the risk and try it, or be left in the dust. How do we embrace the best qualities of this merchant’s attitude, without holding on to presumed beliefs about the customer too closely? 

With experience in our roles and companies, we often see what’s right and wrong; we get this crystal clarity about which ideas are awful, those that cannot possibly work. We develop a powerful intuition that goes off when something’s wrong, saving the team weeks, months, by just calling it. And yet, this same conviction can cause rightful indignation, contempt and lead to a “fixed mindset,” a frame of mind that traps us into thinking we know everything there is to know. This is how teams stagnate. 

When a person’s livelihood depends on something, she develops energy, hunger, passion for winning. The narrower the routes to survival, the stronger her passion — said plainly, hungry artists paint way better. This is why first-generation immigrants are vastly over-represented in tech: they see entrepreneurship as one of their only ways to survive. Furthermore, this is why we keep hearing of top university dropouts who do so well as founders: they just can’t fathom giving up because they’ve sacrificed too much. This same attitude, though, can make us too immersed in the details and drive us to be unforgiving to our teams (we made a mistake? a self-inflicted problem?! argh!!!). This, of course, makes us less effective leaders, as teams will begin fearing failure, as anger acquiesces any of their experimental thirst. That’s a lethal recipe for any company. 

Let’s explore what this concept of balanced, tempered ownership might look like for a well-tenured leader: 

1. Hold your beliefs about customers somewhat loosely

Ask yourself: when was the last time I was dead wrong? When I thought the customers would love it and they hated it? When I thought a particular approach would solve something and it didn’t? If you’re struggling to recall that last time, or it was more than 6 months ago, you might be suffering from the sharpshooter fallacy — try something, see what the results are, find some metric that’s working, claim success. This is surprisingly common: if Swedish health authorities can fall victims to this, so can you.

2. Allow others to challenge your intuition

When was the last time you thought something was a bad idea, but you allowed it to proceed anyway? When you allowed the intuition of those on your team prevail over yours? Can you recall a time when they were right, and you learned something? If these are tough to answer, you may be operating as a take-it-or-leave-it boss. There may be talent and creativity in the organization you could tap into, if only you allowed more space. 

3. Have the patience to try and fail

What was the riskiest thing you and your team tried in the last 6 months? What was the last time you tried something and failed? You can be sure that the most innovative companies in the world — companies that make up the FAANG — are trying and failing all the time. The fabled quote that I’ll paraphrase is right: the best way to have a great idea is to have a lot of ideas. Look at the top 10 Amazon failures, recall Facebook’s dead-on-arrival search engine, Netflix’s Qwikster blunder and the now-defunct Google+. Each of these giants is constantly taking bets, big and small, because it’s in their cultures. It must be in yours too if you want to dominate your space.

Further reading: one of the prominent tech writers of the early 2000’s, Erik Sink, published a blog post 15 years ago that is still one of my favorites on the topics of trying and failing: Make More Mistakes